Head of Sales
On-site · Toronto, Ontario, Canada
Job Summary
Head of Sales to define and execute the company’s sales strategy, close high-value Tier 1 accounts, and build scalable revenue engines. You’ll serve as a player-coach, personally closing key deals while creating playbooks, quotas, and a high-performance culture. Own revenue targets, manage a pipeline across mid-market to strategic accounts, recruit and coach AEs/SDRs, implement rigorous CRM practices (HubSpot/Salesforce), and translate customer feedback into product and go-to-market improvements. This senior leadership role partners with the CEO to shape commercial strategy and drive AI solutions adoption in HOA and multifamily property management.
Required Qualifications
- 8+ years of sales experience, with at least 3+ years in a leadership role at a high-growth B2B SaaS startup
- proven history of consistently exceeding multi-million dollar quotas
- experience building sales departments from scratch—you know how to set commissions, define territories, and implement a sales tech stack
- exceptional ability to present to owner-operator executives, making the value of AI tangible and urgent
- data-driven leadership using CRM data to identify bottlenecks and pivot strategy in real-time
- startup grit and comfort with ambiguity
- PropTech or Real Estate experience is a bonus
Desired Qualifications
- 8+ years of sales experience with at least 3+ years in a leadership role at a high-growth B2B SaaS startup
- proven history of consistently exceeding multi-million dollar quotas
- experience building sales departments from scratch—setting commissions, defining territories, and implementing a sales tech stack
- exceptional ability to present to owner-operator executives and convey AI value
- data-driven leadership with CRM analytics
- startup grit and comfort in ambiguity
- PropTech or Real Estate experience is a bonus
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